Homosexual oriented bars and night clubs.
I assume that you are referring to men who have used surgery, hormones, and cosmetics to look more feminine. In that case the answer is no - they have no uterus, no ovaries and no menstrual cycle.
There are no answers right now - no one studying crossdressing as a function of biology or environment.
Yes almost completely. By adding male hormones the body will change and removing the breasts. The final operation is making the male genitalia. That will never be exactly as a male though.
First off talk to him, find out what and why he does this - if it's because he thinks he wants to be a girl or is sure that "a mistake was made" then get Son, Mom and Dad to a therapist specializing in gender issues. If he's doing it to feel good (masturbate to) just make sure he keeps it to himself and doesn't involve other family members. If he tells you that sometimes he wants to act like a girl and other times a boy, then enjoy, you have a 2 for 1 special and you have a wonderful child who will be sensitive and kind and generous (as you reward those behaviors) and you have a burly boy who is willing to protect the weak and repair "cars/boats,trucks"/be a carpenter/be a welder/a ...
The heart of the whole thing is love: love requires patience, is kind, caring, gentle, never hurts another on purpose and finds a way for everyone to live together in harmony.